The Journey Of A Seasoned B2C Investor

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Transitioning from one VC to another

Ten years ago, Daniel made a big shift in his career, leaving Gemini after 11 years working there. At that point, he transferred from being one of the seniors there, knowing everyone in the company, every investment they made in their portfolio and being immersed in how everything worked, to being the most junior guy in your company, knowing nothing about the culture and the people he now works with.

“On the one hand - it’s the same job, you just leave one firm and join another, but it’s in very different cultures and organizations, so it takes a minute to leave the previous way you were doing things behind and adapt to a new way”.

The second part of what made it hard to make this shift was leaving 7 companies he had worked with for so long while he was part of Gemini, being so involved, caring about them deeply - it felt for him like leaving his kids on their own.

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But although it was challenging and difficult to make, there’s an advantage and an opportunity in transpiring from one organization to another -

“There’s a window when you come as the new guy, where in the beginning you still look at things in a different way, you have a different angle on things, and then it takes about a year where you merge and mold the different views of the organizations to the best of them both. That period is really important because you can really see things and are able to change things. After that, you lose that window.”

That window of opportunity allowed him to change and add some things to Viola, the new company he was entering, because his fresh take on things was valuable - the people who were working in the company for a long time were already used to the way things were operating, their perspectives were too fixated to be able to see how things could be different for the better.

That change is a two way street, Daniel said, because two years into working at Viola, he was a better investor than he was before. 

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A change is something that is difficult to digest - sometimes we don’t want it and have a hard time coping, but there’s also the flip side of things - getting your hopes up too high, clinging to the idea that one change will make everything so much better, even perfect. We’ll be so different, nothing will be the same - just because we changed our location, our job, our environment. 

Daniel shared about the low point he had to go through during that period of change; having his fantasy burst like a bubble -

“In my mind I said - when I’ll move, I’ll take only the good parts of me, and leave the bad parts behind, and when I’ll arrive into the building, I will be Daniel 2.0. And right then in the first minute I sat in the office - guess who appeared right next to me? - All of those bad parts were there too. You want that one change to be a turning point - but change alone is not enough.”

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Finding the right founders to invest in

Daniel defined VC’s in a punch line:

“find great people that go after great markets.”

Every team has strengths and weaknesses, because we’re people, it’s multidimensional and not just black and white, good or bad, and so the way to look at teams needs to be thorough and in depth -

“investors specifically tend to overscore the outcome. They say - ‘oh, that was a great outcome, so it means that's a great team’ - but let’s hold on for a second, maybe it’s not a good team, they just went after a perfect market.” 

He stressed the importance of the combination between a great market and a great team - one cannot exist without the other, and in the end, even a great team can’t compensate for a bad market - we need the combination of the two.

When we zoomed into the characteristics of a good founder that makes Daniel want to invest in them, he said -

“One of the key dimensions to see an entrepreneur through unrelated to school, background or success is the level of hunger and what’s driving that hunger - if you can see and sense that drive, that need to prove something, that hole that needs to be filled, that’s a great indication for success.”

That hunger comes a lot of the times from pain, but it doesn’t have to. It can also be derived from a positive source, from passion - the important part is that the spark in the eyes and the need to achieve that goal is so strong and deep that it runs through your veins.

Daniel added that a big part of that hunger is also being curious -

“being excited about where the world is and where it’s heading - it’s in the combination of being curious and being willing to fight for it.”

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And from the other side, as investors, Daniel sees the emotional support as a big part of their role, being supportive of the founders and their team when something bad happens and being critical when something good happens - making that rollercoaster of highs and lows more balanced and digestible is a way for investors to bring great value to the founders they work with and their startups in his eyes. 

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The perspective of an investor who’s also father to daughters

As a husband and father to girls, I asked Daniel if it has an impact on his personal and professional life, to which he answers with a smile, that talking about feelings is a big part of who they are as a family -

“it helped me connect to a softer side of me, and I think that connecting to the softer side of you makes you a better listener, and also a better investor.”

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We still have so much work to do to ensure women are getting an equal amount of opportunities as founders and investors - we’re getting better these days, but it’s still not enough. When I asked Daniel what can be done to change that, he pinpointed that a lot of that gap of representations of women in this arena stems from the fact that we’re operating in a world that is defined by the way that men behave. 

He gave an interesting example of the way we deem behaviors like shouting and banging a hand at the table as acceptable, which is considered more manly behavior, while other form of expressing emotions like crying is deemed as supposedly unacceptable in this field -

“I think we need to understand that the way women present startups and talk about startups is different in some ways than men, and we need to understand this language, judge it in a different way and really educate investors on how the different startups behave when they’re led by men versus by women. So I think the best thing is to bring more female investors, and through that we’ll gain and see more female founders being successful.”

In the end, it all comes down to the fact that we just want to be our authentic selves, even at work. Why should we try to be anything else?